tert-Butyl piperazine-1-carboxylate → HCID 178423455, compound

HRID 77100Notes

Reaction equation

Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([C:15](O)=[O:16])[CH2:11][CH2:10]2)=[CH:5][C:4]=1[C:18]1[NH:22][C:21]2[CH:23]=[CH:24][C:25]([CH3:27])=[CH:26][C:20]=2[N:19]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:52]([O:56][C:57]([N:59]1[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]1)=[O:58])([CH3:55])([CH3:54])[CH3:53]>ClCCl>[C:52]([O:56][C:57]([N:59]1[CH2:64][CH2:63][N:62]([C:15]([CH:12]2[CH2:13][CH2:14][N:9]([C:6]3[CH:7]=[CH:8][C:3]([F:2])=[C:4]([C:18]4[NH:22][C:21]5[CH:23]=[CH:24][C:25]([CH3:27])=[CH:26][C:20]=5[N:19]=4)[CH:5]=3)[CH2:10][CH2:11]2)=[O:16])[CH2:61][CH2:60]1)=[O:58])([CH3:55])([CH3:53])[CH3:54]

Participants

Conditions

Temperature: 35 °C

Procedure

Method I—Step a To a vial with [1-[4-Fluoro-3-(5-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidine-4-carboxylic acid hydrochloride (obtained as described in general method 8, step b) (0.10 g, 0.26 mmol) and HATU (0.10 g, 0.27 mmol) in dichloromethane (2 mL), TEA (0.08 mL, 0.56 mmol) and tert-butyl-1-piperazinecarboxylate (0.32 mmol, 0.06 g) were added. The reaction mixture was heated at 35° C. overnight, washed with water (3×2 mL) and saturated Na2CO3 solution (3×2 mL). The crude was then purified by flash chromatography (eluent: EtOAc), and then a filtration on an NH2 cartridge was run (eluent EtOAc), to obtain 0.02 g of the title compound (15%).

Workup

washwashed with water (3×2 mL) and saturated Na2CO3 solution (3×2 mL)
customThe crude was then purified by flash chromatography (eluent: EtOAc)
filtrationa filtration on an NH2 cartridge

Sources & evidence

ORD record: ord-e3874e82526544a18e548bf20ff15cab
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835648B2

Reaction notes

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